What types of businesses or clients should a beginner target on Upwork (or similar platforms) when starting with AI automation?
Accept any and all work on Upwork—think of it as an elevator that instantly connects you to large businesses you’d never meet otherwise. Even as a total newbie, you can land a client doing $10–$20 million a year within a week, giving you a powerful case study like 'I helped a $10 million/year business achieve X, Y, Z.' At this stage, don’t worry about qualifying or tightening the funnel; go broad to bootstrap experience, collect case studies, and start making money. The creator shares a personal example: a friend who jumped on Upwork while he was door‑to‑door went from zero to a legitimate $30 000/month income in three‑to‑four months by maximizing opportunity and landing a big‑ticket client whose needs matched his skill set—something the creator missed while grinding door‑to‑door for $5 000/month.
Nick’s top advice for newcomers to AI automation is to show up daily for an extended period and focus on levers that truly move you toward making money. Key levers include talking to customers and putting yourself in front of 10 to 100 people each day; doing this for a year means contacting between 3,650 and 36,500 people. He stresses that the sheer serendipity of creating your own luck will eventually yield results, sharing his own experience of fundraising for child‑sponsorship charities by talking to hundreds of people a day for months, becoming a local celebrity and receiving party invitations—even without selling anything. He concludes that consistently putting yourself in front of many people will lead to winning.
He says you first need to anchor what a lot of money means. AI automation agencies have the lowest barrier to entry and lowest capital cost—comparable to website design agencies in the late 1990s or social-media marketing agencies in the early 2010s. In this space, a lot of money is probably just a few hundred dollars. Any business outside this vertical will cost significantly more than a few hundred to get up and running over a three-month period, so you should expect to spend money to make money. Regarding your specific situation—bidding for email-setup projects on Upwork—lack of experience isn't a time issue; it takes only a couple of weeks to become proficient with any tool well enough that someone will pay you to save them time. So you should combine learning and prospecting. He recommends doing Maker School's introductory automation agency tutorials to gain foundational knowledge and learn to read the language of the tools. Once you understand the language, you can communicate with AI, use Google to find answers to specific questions, and you don't need to know how to do everything right away. The key question is whether a future version of you could solve this problem in the next couple of weeks—and the answer is almost always yes.
You have a keen opportunity to write on the internet and gain support from people worldwide. Even with a wheelchair you can still use a computer and tools like make.com for drag‑and‑drop automation. Start with the free tier of make.com (up to about 2,000 operations per month) and follow my make.com tutorials. Once you have those no‑code skills, the simplest path to customers is Upwork—a marketplace where people post jobs and already have budget. Respond to those requests, solve their problems, and get paid. The cost per acquisition on Upwork is far lower than cold email or paid ads, so even a modest spend (e.g., $100) can yield $500 in returns. Reinvest the profit to bootstrap: spend $100, make $500, then repeat with larger budgets, growing your income and ability to take bigger risks. This compounds over time, turning modest earnings into substantial income as you reinvest and scale.
No. But you can get away with saying, "Hey, you know, I built this stuff for an AI agency." You don’t need to specify that the AI agency is yours, just that you built it for an AI agency—your own. It’s like pulling yourself up by the bootstraps, which is super cool, and that’s what I recommend. Start there. Visualize it: you start with a project you built for an automation company, then use that to land a gig with a personal trainer company, and so on. Create multiple portfolio pieces or case studies—one for an automation company, one for a personal trainer, and one for an AI agency. With three simple systems you’ve built, you can sell a lead‑gen system that adds, for example, $1,535 in revenue in the first three weeks for a B2B SaaS business. Starting with a modest case study builds credibility, and once you have dollar signs in your case studies, it becomes much easier to attract higher‑paying clients.